Many entrepreneurs experience that make-or-break moment when they can cut their losses or hold on, clinging to the proverb: “It’s always darkest before the dawn.”

For Giant Thinkwell co-founders Adam Tratt and Kevin Leneway that realization came on a “cold, dark and rainy night” in Seattle last January. After spending more than a year working on two failed products, they realized it was time to either shut down or give it one final go.

The two had joined forces in 2010 after meeting at Seattle incubator TechStars. With a career that included helping launch the board game Cranium, consulting at Microsoft, and doing business development for New York-based marketing agency Mr. Youth, Tratt applied to TechStars with plans to build a location-based fitness game for kids. His dilemma: “When I went out to raise money, investors said I needed a tech team, but I couldn’t get the team without the money,” says Tratt, 40. Meanwhile, fellow participants Kevin Leneway and Kyle Kesterson were having the opposite problem raising money for their celebrity-based game idea. A developer and designer respectively, they were told they needed a CEO.

Tratt ditched his original idea and the three went to work on Giant Thinkwell’s first product. “We saw this new world where celebrities had direct access to their fans through Facebook and Twitter, and at the same time celebrity games were hot,” says Tratt. “Our hypothesis was, partner with the celebrities and build the games so they can engage directly with their fans.”

With $600,000 in funding, the team tested this theory with Seattle local Anthony Ray, best known as Grammy-award winning hip hop star Sir Mix-A-Lot. Their Facebook game Mix-N-Match launched in June 2011 with much fanfare. “It was a media extravaganza,” says Tratt. “Jimmy Fallon talked about it on his show, people were writing about it, and Sir Mix-A-Lot’s Facebook fans went from almost nothing to 22,000.”

There was just one problem: “Very few people actually clicked on the game,” says Tratt. The idea was a good one, he says, “but we weren’t the right people to make it happen. It needed to be someone with connections in Beverly Hills, not a bunch of board game geeks.”

Not to be deterred, the team moved on to another idea, FlickMob. At TechStars they noticed a phenomenon of people standing around watching YouTube videos together, sharing links and laughs. “We thought we could recreate this virtually by setting up ‘rooms’ where people could take turns cueing funny cat videos and TED talks,” says Tratt. But, with the exception of a virtual Duran Duran party, the site failed to gain critical mass. “It was like we built this beautiful nightclub and got people to walk past it at 9 in the morning on a Monday,” he recalls.

With two failures in less than one year, and investors growing impatient, things started to implode. The company sent home their developers, and Kesterson packed up his desk as well. “Some of our closest mentors said to pull the plug,” says Tratt. “Others said ‘This is what it’s about, the moment that separates adults from children.’”

They opted for the latter, but rather than continue down the path of social games and social video, Tratt and Leneway decided to push the restart button. “We gave ourselves permission to ask, ‘What would it look like if we just started over?’ What would we build today?’” says Tratt.

The answer was the solution to a problem that had been in front of them all along. “We were constantly pitching things,” he says. “Kyle was a great illustrator who could make the best looking slides, but without him, we were on our own.” Meanwhile, most of their presentations, they realized, were in coffee shops or open workspaces over an iPhone.

The idea: Create a presentation app that makes even the aesthetically challenged look like creative geniuses. “Think about Instagram,” says Tratt. “It takes a crummy photographer and crummy camera and turns us into Annie Leibovitz.”

Tratt and Leneway did a rapid prototype and brought in a third partner, Marc Kamaka. In June, they went back to investors to show them what they’d built. While the product was a rapid departure from a Sir Mix-A-Lot social game, the investors were impressed, so much so they agreed to provide additional funding.

Haiku Deck launched in mid-August and within a couple weeks was featured in the new and noteworthy section of iTunes store and ranked number one for free productivity products. “Downloads in the first two weeks exceeded our one year forecast,” says Tratt.

Haiku Deck lets you choose from one of 16 themes that apply the same fonts and looks throughout the deck. You can upload your own photos or choose images that are recommended based on key words in your text. Once your deck is complete, you can view it on your iPad, embed it on a website or share the link. Although the app is only available for iPad (a Google Android version is in the works), Haiku Decks can be viewed on any device.

While the app itself is free, the company charges $1.99 for certain themes and will eventually introduce premium photography and professional-level upgrades. At the same time the Giant Thinkwell team hopes to win over traditional PowerPoint users, they think Haiku Deck will appeal to anyone looking for an elegant way to share ideas.